As to optically active (-)-2-halo-1-(substituted phenyl) ethanol, the present inventors have not yet seen any patent, report or the like relating to its manufacture. Meanwhile, as to optically active chloro-substituted styrene oxide, there is a report that 72-86% e.e. could be achieved by epoxidation of chloro-substituted styrene by means of Nocardia corallina (Keizo Furuhasi; Organic Synthetic Chemistry, 43, 162 (1987)). Another known method of synthesis thereof is by interphase moving reaction between chloro-substituted benzaldehyde and dimethyl sulfonium methylide, but this method is extremely poor in optical purity attainable (Hiroyuki Sawada; Japanese Laid-open Patent Publication No. 105024/1976.
After having made intensive studies for development of an efficient method of manufacturing optically active (-)-2-halo-1-(substituted phenyl) ethanol and (-)-substituted styrene oxide, the present inventors discovered existence of some microorganisms capable of asymmetrically reducing 2-halo-1-(substituted phenyl) ethanone stereospecifically and converting it into (-)-2-halo-1-(substituted phenyl) ethanol and thus completed the invention.